Water → (3-Bromo-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanol

HRID 549540Notes

Reaction equation

HRID 549540 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][Si:11]([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 577919013-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde

Product 1

HCID 57791917(3-Bromo-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde (7 g, 22.2 mmol) was dissolved in THF and sodium borohydride (0.92 g; 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and water was added, and the reaction mixture was partly evaporated to strip off THF. Ethyl acetate was added and the phases separated. The organic phase was washed with water, dried, and evaporated to dryness. Yield: 6.4 g; HPLC-MS: m/z: 317.0 (M+); Rt: 2.37 min.

Workup

  1. customthe reaction mixture was partly evaporated
  2. additionEthyl acetate was added
  3. customthe phases separated
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a68a4d39cefe45179c33cbb011657172
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

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